Angelheaded Hipsters
by ImagineBackstory
Summary: Three words: Gender-bent Literati.


A/N: Um, gender bender? I don't know where this came from. It's definitely AU, also might be slightly OOC because, well, the characters aren't likely to stay exactly the same if they're the opposite gender. Let me know what you think, if I should continue this? Also, I haven't written in third person or present tense in awhile, so bear with me while I fumble with grammar...

Also, random fact. Apparently Jess was supposed to be around for six seasons, staring in season two and going all the way through till the end as a series regular. But the actor only contracted himself for two years. Lame, lame, lame! They could have ended up together after all! Sigh...what could have been...

**Angelheaded Hipsters**

By Imagine Backstory

_I saw the best minds of my generation destroyed by madness,_ _starving hysterical naked,_ _dragging themselves through the negro streets at dawn looking _ _for an angry fix,_ _angelheaded hipsters burning for the ancient heavenly_ _connection to the starry dynamo in the machinery of night,_ _who poverty and tatters and hollow-eyed and high sat up smoking _ _in the supernatural darkness of cold-water flats floating _ _across the tops of cities contemplating jazz..._

He's just started reading his favourite poem for the fortieth time when he hears his mother calling his name. "Yeah?" he yells back, hoping his voice carries out to the foyer.

"They're here!" Lorelai Gilmore shouts. He can hear the muffled voices in the hall to prove it. He hasn't forgotten about their dinner guests, but he was hoping for another ten minutes of peace so as to get fully engrossed in _Howl._

Closing the book, he sets it gingerly onto his desk. "Coming!" He stands, but they are now in the kitchen, right outside his bedroom. He glances briefly into the mirror hanging on the door of his wardrobe, wondering fleetingly if perhaps he looks a bit too nerdy like this. His short brown hair styled _just so_ on top of his head, the sleeves of his white shirt poking out from underneath his plaid button-up shirt, his dark plastic-rimmed glasses perched between his light blue eyes. A the last minute, he decides to unbutton the plaid shirt and push the sleeves up to his elbows, and lose the glasses. Much better.

"Rory?" Lorelai peeks her head into his room, taking in the sight of her son primping in front of the mirror with a smirk. "This is Jess." He turns towards the door as a slight, dark-haired girl appears there. She's wearing a tigh-fitting long-sleeve waffle shirt with a camo print and jeans that looks like they're from the guys' section of the store, and her heart-shaped face bears a look of permanent nonchalance. But her presence fills the room before she has even fully stepped foot in it. "Jess, this is my son, Rory." Introductions done, Lorelai disappears as Jess takes a step into Rory's room.

"Hi, I'm Rory," he says, raising one hand in the fashion of waving.

She merely glances at him. "So she said." She wanders over to his bookshelf, skimming the tip of her fingers along the spines. "Rory short for anything?" she asks.

He shrugs one shoulder. "Uh. No. Just Rory. Inspired by my mom's name, I guess. Kinda."

"Huh." She leans closer to one of his books and pulls it off the shelf. She just glances at the back cover before setting it down.

Rory watches her as she takes her time taking in all the little nicknacks in his room. Her dark hair is slightly curly and whispy, falling to just past her shoulders. She's lean and catlike in her movements, which only adds to her commanding presence in the room. She demands to be noticed, even if it's not intentional. She's also quite small, he notes, guessing that she probably will come up to his shoulder if she were to stand next to him. "So, Jessica or Jessie?" he returns the question.

The corner of her mouth lifts briefly in the tiniest of smirks. "What makes you think Jess is short for anything?"

He makes a face. "Because no self-respecting mother simply names their daughter Jess."

There's now a wicked smile on her face, one side of her mouth slightly crooked. "Jessica. But _no one_ calls me that." She turned away. "But you're wrong about one thing. My mother is no self-respecting woman."

He snickers lightly. "So. Jessica Danes."

"Mariano."

"What?"

She looks at him like _duh. _"Jessica Mariano. My father's name?"

"Oh. Right." He flounders about dumbly as she lingers by the stack of books on his nightstand. "You read?" he asks, reaching for something to say to Luke's niece. He's a little taken aback when she takes several steps towards him, officially invading his personal bubble as she stands merely a foot away, her fingers skimming the surface of his desk. She doesn't seem bothered by the proximity, however, so he holds his ground, suddenly determined to have the upper hand. He does note proudly that his guesstimation was accurate; the top of her head barely clears his shoulder and their difference in height will allow for perfect embracing conditions. Unsure where such a thought came from, Rory shakes his head to clear it, feeling his face grow hot.

Oblivious, Jess picks up the copy of _Howl _he'd been reading at his desk. "Not much," she bristles, flipping through the poem. Rory isn't sure if she's just flipping through or if she's actually skimming the pages with her molten hazel eyes. Pretty eyes, he notices off-handedly, and he feels his palms getting sweaty. He wipes them on his jeans as she moves towards the window, brushing her shoulder against his chest. "These open?" she asks, fingers curling around the latch.

He's completely encaptured by this girl, this dark beauty before him. "Yes," he says.

She shoves upwards, and the window slides open with a groan. "Let's go." She lifts herself into the windowsill, ducking her head to avoid hitting it on the window frame.

Mustering his courage, he steps forward and leans his elbow on the window frame, leaning down towards her. "Not a good idea," he says quietly, glancing over his shoulder. "Dinner's almost ready."

"Doesn't matter, if we're bailing," she shoots back, the warm light from his bedroom gleaming in her dark eyes. She's sinking backwards slowly; her foot curls around his calf to prevent her from falling out completely. She smirks as he glances over his shoulder once again. "You always do as you're told, Rory?"

Unappreciative of her condescending tone, he steps away, satisfied when she nearly topples out of the window. "Sookie's made a really nice dinner for you and Luke," he says, stuffing his hands in his pockets. "It'd be really rude to just leave."

Her gaze lingers on him as he stands awkwardly in the middle of his room. He shifts uncomfortably, feeling the weight of her stare. Finally, she pushes off the windowsill and drops onto the carpet, pulling the window closed behind her. "Fine, Mama's boy," she snickers as she brushes past him and out of the room.

With a private grin, he follows her out. "Want a drink?" he asks, going to the fridge and helping himself to a soda.

"I can get it," she says, but he's already tossing her a can. She frowns as he cracks his open, his eyes crinkling in a smile as he takes a long sip. "I was going to grab a beer."

He swallows, passing a hand over his lips. "I know." He gestures towards the living room in an _after you_ like fashion, biting his lip when she scowls and stalks by him indignantly, only it's not in the direction he had suggested. She lets herself out onto the back porch, letting the door slam behind her.

Lorelai sticks her head into the kitchen. "You kids ready to eat?" Seeing only one teen in the room, she frowns. "Where's Jess?"

Rory nods towards the kitchen door, rolling his eyes. "She's not keen on dinner."

"Huh." Lorelai places a hand on her son's shoulder as she heads for the door. "I'll see you in there, okay, kiddo?"

"I can talk to her if you want," Rory offers, but Lorelai is already waving him away.

"Let the girls talk," she says, letting herself outside.

Shrugging, Rory heads into the living room.

* * *

The next day, the diner is crowded as usual with the morning rush. Jess leans against the counter as she gathers her thick hair into a messy bun, careful to avoid knocking the pencil propped behind her ear. Luke appears from the kitchen, a tornado of action as he squeezes past his niece and goes to grab a doughnut from the dome. "Prep some more coffee," he says gruffly, shoving the glazed pastry into a white paper bag.

Jess glances over her shoulder at the freshly brewed pot just sitting there. "I just brewed coffee."

"Gilmores." Luke nods towards the window. "They'll clean us out."

Sure enough, as Jess turns the bell over the door dings brightly, announcing the arrival of two such Gilmores. Lorelai greets Jess curtly before wandering off to flirt with Luke. But Jess' eyes are on Rory as he grabs a table by the window, letting his heavy backpack drop with a thud onto the floor next to his chair. It's a miserable day outside; she watches him watch the first few raindrops spatter the pavement. Her eyes scan quickly over his body, taking in the sight of the trim uniform, complete with a navy blazer and tie. He's cute, she notices suddenly, her gaze sliding over the gentle slope of his jawline and the lines of veins running beneath the taut skin of his forearms.

Pressing the brew button on the coffee maker and grabbing the pre-made pot, Jess wanders over to Rory's table, placing an empty pink mug in front of him and delighting in the fact that he jumps slightly at the noise. "Well if it isn't Just Rory," she says, tipping the pot of coffee so as to let the inky liquid slosh into the mug.

His eyes widen slightly as he stares up at her, surprised to see her donning an apron and order pad. "Well if it isn't Not-Jessica Mariano," he retorts, wrapping his fingers around the steaming mug to warm them. His eyes dart every-so-briefly down to her narrow hips as she shifts her weight; she has terrible posture, he realizes, noting the slanted curve of her lower spine. And she's so _thin_. Like a ballerina. "Do you dance?" he asks, the question surpassing his lips before he can filter the thought.

Amusement alights in her dark eyes. "Do I look like a dancer?" He takes a sip of coffee to hide most of his face. But his blue eyes peek up at her over the rim. As he sets the mug down, he shrugs one shoulder. Jess slowly passes her tongue over her full bottom lip, noticing the way his eyes follow the movement. She braces herself on the back of his chair as she leans down towards him. "I don't dance."

"Much?" The corner of his eyes crinkle as a smile widens over his face. When she frowns, confused, he points to her hips. "I'd have let you borrow it if you'd asked," he says brightly.

She blanches and reaches for her back pocket, where she only now remembers she left Rory's copy of _Howl. _She removes it and tosses it onto the table in front of him, chuckling as she fixes him with a sultry stare. "Checking out my ass, Gilmore?"

His cheeks turn a delightful shade of pink. "Thief," he says. He flips the book open and his face falls. "Did you _write_ in this?"

"Maybe."

"You vandalized my book."

"You asked me if I _dance_."

He shakes his head. "How are those things even on the same level?"

"I know, right?" She places a hand firmly on her hip. "The book should be collateral for what you've done."

"Excuse me, but you stole my book _before_ I asked you if you dance." He's still holding the book open, but his large hands are splayed out, permanently asking a silent question. "And what's wrong with that question, anyway? You should take it as a compliment. Ballerinas are beautiful."

"Wow, I've graduated from dancer to full-on ballerina, hey? I must be getting good." She shoots him a charming smile, turning her body away from him. "Enjoy the notes, Just Rory."

"Thanks, Dodger."

She pauses, turning back towards him, her mouth slightly open as she sticks her tongue between her teeth. "You're welcome, Nancy."

He looks up, surprised, but she's disappeared into the kitchen.

* * *

"I don't know what Luke was thinking, agreeing to take her in like this," Lorelai chirps as she sets the Chinese takeout bags down on the coffee table. "He doesn't know the first thing about teenaged girls in general, let alone how to raise one."

"She's seventeen, Mom," Rory says, helping his mother to removed various containers of sizzling food. "She doesn't need much raising at this point. Plus, aren't girls supposed to mature sooner than boys? I mean I thought girls hit their troubled teen years around thirteen or fourteen, whereas guys cause grief by age sixteen or so."

Lorelai blinks then narrows her eyes at her son. "Do I need to worry about you, then?"

He laughs. "Have you ever?"

"No, I suppose not." She digs into the sweet and sour pork. "That girl is not normal, though, Ror. I mean, you should have heard the way she talked to me the other night. She's a piece of work."

"That she is." Rory slurps up some chow mein. "Cut her some slack, though. She's angry, she's misunderstood, she's in a strange town where she doesn't know anyone. Stars Hollow is probably a lot to handle for an outsider."

Lorelai tilts her head forward, incredulous. "Are you _defending_ her?"

He shrugs, frowning. "Sure. I mean, did you deserve to be treated like that? No. Does Luke need the extra hassle? Of course not. But it is what it is, and I really don't think getting all _burn the witch at the stake _is going to help matters for anyone."

Lorelai shakes her head and clicks her tongue. "Whose kid are you again?" she asks, sinking back into the couch. "God, sometimes you remind me so much of your dad."

"Should I be offended...?"

"No, honey. Fortunately, you got your father's chivalrous nature towards young women. It's okay, though. You get your good looks from me, and that's what counts." She reaches out to affectionately toussle his hair. He laughs, cowering into the corner of the couch to protect his hair from mussing. When she relents on her attack, her face becomes serious. "Guess I don't need to ask you what you think of Jess?"

She's fishing for information, her tone light and too conversational. Privy to his mother's ways, Rory makes a face. "I really don't know her. I only met her yesterday. What I said is just what I've gathered over the past twenty-four hours."

She picks up on his defensive tone and raises an eyebrow. "Just saying, I've never heard you defend someone so unconventional so quickly."

"How is she unconventional?" Rory asks rather incredulously. "She seems pretty normal to me."

His mother scrunches up her face as she searches for the right words. "She dresses like a boy," she points out. "And she's abrasive. And crass. Like I said; you should have heard how she talked to me when they came for dinner last night."

"So she's a tomboy with no filter," Rory says, waving his mother's comments aside. "That's hardly unconventional."

"It is around here," she counters. Rory raises his eyebrows in reluctant agreement. Point for Lorelai. "I didn't even tell you the best part of last night," she continues, spearing some kung-pow chicken on a single chopstick. "After my chat with Jess I tried to offer Luke some friendly advice. Cuz, you know, he's never raised a teen before, whereas I consider myself to be somewhat of an expert in that field."

Rory gives her a pointed look over his forkful of chow mein. "You've raised a teenaged boy. Girls are different."

"Well, then, I'm an expert on _having been_ a teenaged girl," she corrects, indignant.

"No, you're an expert on having been a teenaged mother, if there is such a thing," Rory flips, giving his mother a cheeky smile.

She smacks him, hard, on the knee. "Shut it," she snaps, but her eyes are twinkling, "and let me finish, will ya? Anyway, so I try to offer some advice and you know what he does? He gets all angry and tells me to mind my own business! Can you believe it? There I was, just being a friend, trying to help another friend out, and he got _mad_!"

Rory finishes chewing and swallows before speaking. "Well, you know Luke, Mom. He's stubborn. He likes to be in control, do things his way. He probably just didn't appreciate you pointing out that he might be doing something wrong."

Her mouth falls open as she glares at her son. "Are you going to take my side at all tonight?"

He holds his chopsticks up in surrender, raising his eyebrows innocently. "Sorry, Mom. You know I'm always on your side. I'm just trying to make you see the other side, too."

"I don't _want_ to see the other side," she whines, flopping back into the couch. "I just want to bitch to my son and have him agree with me wholeheartedly so we can move on and eat copious amounts of greasy Chinese food and watch terrible movies!"

He sighs, relenting. "Okay, Mom. You're right. Jess is unconventional and Luke is irrational. They both suck. That better?"

She pouts at her food. "Yes." A moment later, "No."

"See. Me agreeing with you is not always the best thing."

"That's because you already pointed out all the flaws in my arguments!" she protests, lightly kicking his leg. "Evil child. You're not supposed to be wiser than me."

"But I have your good looks," he reminds her with a charming smile, "and that's what matters, right?" He cowers away to avoid the onslaught of limbs as Lorelai playfully attacks her son, laughing the whole time.

* * *

Jess watches with an amused smirk as the crowd outside the market grows and the expressions on people's faces change from confused to terrified when they realize what they think is happening. From her vantage point leaning against a streetlamp pole in the square, it all looks like some sort of staged scene from a PBS murder mystery. _Was it Colonel Mustard with the crow bar in the billiard room? _She can't help but snicker as the simplicity of her trickery manages to stump an entire township.

When she spots Rory joining the crowd, however, her face falls a fraction, anxious to see his reaction to the prank. She knows he's smart enough to realize that it is, in fact, a prank. She watches the tall, slender boy as she peers over the shoulders of his peers, his expresson ardently curious. It's only then, as he leans forward to get a better look, that Jess catches sight of a willowly girl standing next to him, clutching his arm for support as she gets up on her toes, trying to get a better view herself. She's tall—nearly as tall as Rory, and that's saying something—with soft brown hair that she has pulled back in a conventional ponytail. She's not wearing the same uniform as Rory, so Jess deduces she must attend the local high school; though that says less about her intelligence level and more about her financial status, as evident by the worn Chuck Taylor's on her feet that appear to be falling apart.

Not that Rory bought his way into prep school—Jess has heard Luke go on and on about the boy's smarts too many times to know that it was his brain and his brain alone which got him that coveted spot. Though—she imagines he probably had financial help from his grandparents, who Jess has learned through overheard conversation are loaded socialites. While Jess maintains a steady presence in a room, people often tend to forget she's there when they speak, allowing her to bear witness for all sorts of tidbits of information she may or may not care to know.

What she does care to know, however, at this particular moment in time, is who the model-esque Cinderella who's hanging off Rory's arm is. He hadn't mentioned a girlfriend—not that Jess had asked, nor does she care. But it gives her the upper hand, something to dangle in his pretty little face. Her singularity renders her immune to classic high-school-level taunting in the romance department; the same cannot be said for Rory, if the other girl in fact is his girlfriend.

She quickly thanks her past-self for choosing to wear red today. When Rory glances up he spots her immediately, and she offers her most shit-eating smirk, smeyezing him up. He knows it's her doing instantly, his face contorting into a disapproving scowl. She is delighted that she can cause more of a stir than the town's boy-wonder.

When the cops show up the clear the crowd out, Jess lopes across the street to join Rory and mystery girl on the sidewalk. Sticking her hands in her pockets, she kicks at a loose pebble on the street. "Insane, huh?" she asks, nodding towards the chalk outline of a body on the sidewalk. "I mean, I could do a head count of the entire town right now and tell you everyone is accounted for. Which means the victim was an _outsider._"

"You mean like you?" Rory retorts, narrowing his eyes.

Jess laughs. "Good one." Her gaze shifts to the girl next to him, who is regarding Jess somewhat coolly. "Girlfriend?" she asks Rory.

"Of course," he says, placing a hand on the girl's back. "Dana Forrester, this is Jessica Mariano. Jess, Dana. My girlfriend. Jess is Luke's niece from New York," he adds by way of explanation of Jess' presence in Stars Hollow.

Jess nods to Dana. "How you doin'?" Regarding Rory once more, she narrows her eyes. "Call me Jessica one more time and I will pants you so hard you might as well be wearing a jockstrap."

"Big words from someone who's got the whole town in an uproar," Rory retorts, folding his arms across his chest.

Dana's eyes widen. "You did this?" she asks Jess incredulously. She is very pretty, which annoys Jess inexplicably. The way her arm curls around Rory's protectively only furthers Jess' irritation.

Jess raises her arms innocently. "Whoa, get me off this firing squad! What makes you so sure I did this?"

Rory rolls his eyes. "I can't think of anyone else who would."

"You don't know me that well," Jess shoots back, raising a skeptical eyebrow. "You've no idea what I would or wouldn't do."

"Whatever. Come on, Dana. I'll walk you to school." Rory slings an arm over Dana's shoulders as he leads her away towards Stars Hollow High, shooting Jess a disdainful look over his shoulder as he goes.

Jess drags on her bottom lip with her teeth as she half-smiles, checking Rory out as he strolls away from her. She pulls her small notepad out of her back pocket, flipping to the page where she had messily scrawled a passage from the book she had "borrowed" from Rory.

_...with dreams, with drugs, with waking nightmares, alcohol and cock and endless balls,  
incomparable blind streets of shuddering cloud and lightning in the mind leaping toward poles of Canada &amp; Paterson, illuminating all the motionless world of Time between..._

She snickers at the thought of Rory reading certain passages from this particular poem. Some of it is quite explicit; Jess knows from having read it in its entirety about forty times over. She can't imagine a goody-two-shoes like Rory getting a kick out of this kind of poem. Jess pictures the delightful shade of pink his cheeks must turn when he reads it, blossoming over his neck and collarbone, descending down his breastplate...

Shaking her head, she pockets her note pad once more and, shoving her hands back in her pockets, proceeds with skipping school, heading instead for the park on the outskirts of town.

BREAK

A/N: So, I realize this is incredibly weird, and I've never seen it done before. Then again, I'm still relatively new to this forum, so I apologize if it isn't in fact original. In any case, let me know what you guys think, if you want me to continue I gladly will, because this was actually really fun to write. But of course I still have to work on my other story, Eight and a Half! Also, as you probably figured out, the poetry mentioned is from _Howl, Part I _by Alen Ginsberg.


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